Not the recurring roles in multiple streaming shows. Not the dozens of smaller comedic parts, in which she holds her own brilliantly against everyone from Andy Samberg to Jennifer Aniston to Blink-182. And certainly not the millions of views and hundreds of thousands of followers on Instagram and TikTok. Heck, Gilroy wasn’t even supposed to move to Toronto, let alone Los Angeles.
No, for the 34-year-old comedian and actress — whose latest TV project, as part of the cast of Interior Chinatown, comes to Hulu next month — the original goal was simple: teach high-school drama in Edmonton.
“I thought, if I want to live a playful, goofy life, the closest thing I can imagine is being a drama teacher,” Gilroy says in a recent phone interview.
She nearly got there, too, even completing her final practicum at Archbishop MacDonald High School. But then she misread an email while hiding in the darkness in a wizard’s costume, and everything changed.
Like pretty much everything Gilroy does these days, it’s a funny story.
Gilroy, grew up in south-side Edmonton, and like all true children of the ’90s, still refers to where her family members live by how far they are from the nearest mall. As a kid, her dad introduced her and her sister to the comedic stylings of Monty Python and the Austin Powers movies, and later on Gilroy became even more inspired by the women on Amy Poehler–era Saturday Night Live and The Sarah Silverman Program.
“I’m really drawn to comedy that’s mischievous and playful,” Gilroy says. “I like to watch people have fun when they perform — like when Sarah Silverman pulls out a guitar and sings about pooping in a mall.”
By her own admission, Gilroy wasn’t much for children’s activities. Her defining memory of her time in Girl Guides was the time she ran around the gym, knocking everyone else’s hula hoops down (“Just a bone-chilling level of annoying,” she says now). But if her attention wandered whenever there were too many rules to memorize, Gilroy quickly locked in on the idea of performing for others, especially in settings where she could follow her intuition.
During story time at Keheewin Elementary School, she would bring in magazines from home and make up elaborate stories about the women in the yogurt ads. Later, onstage at Strathcona High School, Gilroy remembers being so caught up in her first formal improv scene — three witches cackling overtop of a cauldron, a classic — that she had to actively hide how excited it made her feel.
“I walked offstage and thought, Uh-oh, need to do that again,” she says.
Still chasing that high after graduation, Gilroy started performing at shows with Grindstone Theatre Society. But she still couldn’t see a viable path to becoming a professional goofball in Edmonton. Instead, Gilroy enrolled in the Faculty of Education at the University of Alberta, only agreeing to turn it into a combined degree with theatre at the urging of an insistent professor, Alex Hawkins.
Her entry into the entertainment business was about as fluky as it gets. In early 2014, two of her colleagues at Grindstone came across an open casting call for the host of an upcoming prank show on YTV, and asked Gilroy if she would help them film their auditions. It all seemed like a fantasy to Gilroy — what were they going to do if they got the part, move to Toronto? — so she ended up taping an audition of her own, too. Because why not?
At the time Gilroy was working part time at the Telus World of Science’s Harry Potter exhibit, and one evening she got a message containing what she thought was bad news.
“I was literally crouched in the dark, in my wizard’s robe, and I got an email from a casting director in Toronto, asking for another tape,” Gilroy says. “So I texted my girlfriends — oh god, I was so green — and said, ‘Gals, there’s something wrong with our tapes. We gotta re-tape them.’”
When her friends told her, confused, that they did not receive this email, Gilroy did some Googling — at which point she figured out what a call-back was, and that this was actually very good news, albeit only for her. So, she sent in another tape, and booked the job. At which point she did what had very recently seemed impossible: she packed her bags and headed to Toronto.
“When I left Edmonton, I said, ‘I will be back, 1,000 per cent guaranteed,’” Gilroy says. “And now, blink, and it’s been over 10 years.”
In fact, Gilroy still planned to come home immediately after filming the first season of Undercover High. But then the show got picked up for a second year. And from there she was hired to be a host for YTV’s flagship kids’ show, The Zone, which she did for another four years while doing guest spots on adult comedy shows like Royal Canadian Air Farce and The Beaverton.
Meanwhile, in the evenings, Gilroy became an attentive student for the first time in her life. No longer the teenager who showed up late to classes at Scona while wielding a giant Booster Juice, now Gilroy was immersing herself in the world of improv through the famed Second City theatre group. She took as many classes as she could, and eventually got accepted into the touring company.
Within a couple of years, however, Gilroy noticed that many of her favourite performers in the group seemed to hit similar walls in their careers.
“I was like, ‘Why aren’t these women getting their own TV shows?’” she says.
Gilroy started reading memoirs by American comedians, and realized that the Upright Citizens Brigade in Los Angeles seemed like a much more reliable springboard into long-lasting success. Again, it seemed like a fantasy, but she filled out her green-card paperwork anyway — and got approved. It was 2018, and now Gilroy found herself moving to southern California.
Success came just as quickly in Hollywood as it had in Toronto. While continuing to hone her improv skills at Upright Citizens Brigade and the Groundlings, Gilroy made her first appearance on American network TV on Brooklyn Nine-Nine, as a bachelorette-party attendee who accidentally eats part of her feather boa and — spoiler — pees in a garbage can. Not long afterwards she was cast in a recurring role on a season of Netflix’s Glamorous (ironically filmed back in Toronto). Amidst her TV work, Gilroy has also rapidly become a fixture of the comedy-podcast circuit, reliably brightening up every episode of Comedy Bang Bang (or podcasts like Whitney Cummings’s Good for You or Andy Richter’s The Three Questions) in which she appears.
“There are a lot of pinch-me moments,” Gilroy says of her L.A. résumé to date. “A couple of months ago I did improv with Seth Rogen at the Hollywood Bowl for 8,000 people. I did History of the World, Part II, and Mel Brooks was at the premiere. Danny DeVito played my dad — or rather, I played his daughter. No wonder I always assume I’m in a coma, and none of this is really happening.”
And yet it’s the smaller parts and videos, with their inherent shareability, that have played an equal role in Gilroy being named a “Comedian You Should and Will Know” by Vulture in 2022. A one-minute clip from her appearance on an episode of Jury Duty, as a vapid-yet-committed brand ambassador, has been circulating social media for more than a year. So, too, have the short comedy videos Gilroy started posting on her own accounts during COVID lockdowns, taking character types like Snobby L.A. Retail Girl and 5th-Grade Boy at a Fair (K-Days being an obvious inspiration on the latter) and twisting them into brilliant, deranged new shapes.
Gilroy returns to streaming TV this November with Hulu’s adaptation of Interior Chinatown. Executive produced by Taika Waititi (What We Do in the Shadows, Jojo Rabbit), and adapted by Charles Yu from his own acclaimed novel, it’s about an Asian-American waiter, played by Jimmy O. Yang, who witnesses a crime and suddenly finds himself the main character in a very different story.
“It’s an incredible book, very fun and genre-bending, and the show is just like that,” says Gilroy. “I play a ‘90s-vibe-law-and-order detective — which means I get to wear a lot of low-rise jeans, and have a gun.”
As she enters her second decade abroad, Gilroy still doesn’t quite believe all that she’s been able to see and do. But she’s managed to stay level-headed through it all — a mentality that she is quick to chalk up to her hometown.
“Being from Edmonton is a very grounding force, in the best way,” she says. “To have this whole other lifetime of knowledge and experience has really made this fun, and not feel like it’s life or death.
“To me, everything has felt like a cherry on top,” she adds. “Did I feel like I made it when I went to Toronto, or L.A.? I wasn’t ever trying to make it! Everything was 100 per cent surprising, 100 per cent thrilling. It all felt like a bonus — and it still feels that way. I just wanted to be a drama teacher.”
At this point, though, it seems less and less likely that Gilroy is going to use that degree.
This article appears in the October 2024 issue of Edify
